


Swallowing my Pride

by TrueBlue08



Category: The Office (US)
Genre: Anal Fingering, Anal Sex, BDSM, Blow Jobs, Bondage, Butt Plugs, Coming Untouched, Contracts, Cunnilingus, Dirty Talk, Double Penetration, Electricity, F/M, M/M, Nipple Clamps, Punishment, Rape/Non-con Elements, Sub Jim Halpert, Urination, Voyeurism
Language: English
Status: In-Progress
Published: 2017-02-15
Updated: 2017-06-12
Packaged: 2018-09-24 18:51:11
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 6
Words: 13,672
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9780425
Author URL: https://archiveofourown.org/users/TrueBlue08/pseuds/TrueBlue08
Summary: With Dwight as the newly appointed Manager of Dunder Mifflin Scranton, Jim knows his job is in danger. Dwight agrees to renegotiate his employment contract, if Jim can swallow more than just his pride...





	1. Chapter 1

**Author's Note:**

> More chapters to come at a later date. Nothing racy in this chapter, just setting up the story. Please leave comments especially which parts that you like, this is my first work on here, so let me know how y'all like it.

“Jim, I need to see you in my office,” Dwight called to Jim. Jim immediately groaned, Dwight had only been made interim manager of Dunder Mifflin Scranton a few days ago and already he was making life at work unbearable. Pam reached her hand out to lay it on top of his, and the two held each other’s eyes for a moment. Though she tried to hide it, Jim could see the worry in her eyes. Rumors had been circulating all morning, that Dwight had finally received permission from Jo to fire people if he deemed it necessary, and Jim had a sinking feeling he would be out of a job before lunch. Normally, this wouldn’t have bothered him too much, his life’s ambition had never been to be a paper salesman, but his and Pam’s combined paychecks were barely keeping their family afloat. If he was out a job… Sighing, Jim swallowed his pride and stood up, heading into Dwight’s office, resolving himself to do whatever he needed to for his family.   
“Jim, Jim, Jim” Dwight started. “Close the door”. Dwight was happier than Jim had ever seen him. Jim sat down in the chair after closing the door behind him.  
“Dwight, if I could just start by saying-“ Jim started, readying himself to start begging  
“Don’t bother, you’re fired” Dwight laughed ecstatically. “You have no idea how long I’ve been waiting for this moment. All those pranks but I am the winner now!”  
Jim sat quietly for Dwight to calm down. “Dwight, I really need this job,” he began quietly. “Pam doesn’t make nearly as much on commission as I do and our family really can’t afford to lose this income. Dwight please, I’ll do anything,” Jim’s words became hurried and shaky the more nervous he got. “Please Dwight, I’ll move to the annex, I’ll clean the bathrooms, but I have to keep this job.”  
Dwight sat back in his chair, his smug look fading into one of deep calculation, as though he’d just been offered a business deal that was too good to be true. Jim waited to hear Dwight’s rejection, but it never came.  
“Come over to Schrute farms after work, we’ll have a beer and discuss this. I think I just might have a job or two for you.” Dwight said, turning his attention to the papers on his desk. “You may leave”.  
And just like that, Jim was dismissed and sitting back at his desk, his head spinning at the complete 180 that meeting had taken. Pam looked worried at his expression, ‘Fired?’ she mouthed at him. Jim gave the slighted shake of his head, and Pam, looking very relieved, went back to work. Jim however was unable to work all day, thinking of the conversation he would have with Dwight later. What would Dwight want him to do?

 

Jim walked reluctantly to Dwight’s door and knocked.  
“Come in,” Jim heard Dwight shout from inside. Pushing the door open, Jim made his way toward the kitchen, remembering the time he had spent the night here with Pam. In the kitchen, Dwight was waiting with two opened beers.  
“Hey man, I just wanted to say thanks for agreeing to talk about this, I really appreciate it,” Jim started, taking the drink that Dwight handed him. Taking a sip, Jim noted the bitter flavor ‘Weird Pennsylvania Dutch home brew’ he thought to himself.  
“Jim, please, I am a reasonable man. Let’s have our beer and then we can talk about matters of business.”  
The two made small talk for about 10 minutes as they slowly drained their beers. Jim had begun to feel a bit light-headed, having never been much of a drinker in the first place. ‘Wow all those nights at home have really shot my tolerance,’ he thought to himself.   
“Now Jim, when you said that you would do anything to keep your job, did you mean it?” Dwight asked, shifting closer to Jim.  
Jim nodded, and then stumbled, barely able to keep his head straight. He leaned against the countertop for support.  
“Oh Jim, you have no idea how happy I am to hear that. I hope you don’t mind but I’ve taken the liberty of drawing up a new employment contract for you.” Dwight unrolled a piece of paper. “If you look, you’ll see that you will retain your current salary plus commissions and you’ll even be able to stay on as a salesman and keep all of your current clients. It also spells out a few extra responsibilities you’ll have to take on, nothing too much though, I’m sure you won’t mind. If you could just sign here,” Dwight indicated a line at the bottom of the paper. “Be sure to read through the agreement first”  
At this point, Jim’s head was spinning, he couldn’t even read the title of the contract, let alone the fine print at the bottom. ‘This sounds like a good deal’ he thought as he took the pen from Dwight and sloppily signed his name at the bottom.  
“Perfect, let me just go scan a copy of this and then I’ll be right back,” Dwight said with a dark smile. Before Dwight had even left the room, Jim sank to the floor and passed out.


	2. Chapter 2

**Summary for the Chapter:**

> This is where is starts to get good, Jim/Dwight

Jim awoke in a dimly lit, musty room. ‘Oh man, what time is it’ Jim thought to himself, going to turn over before realizing that he couldn’t. He had been bent over some sort of barrel with his hands and feet bound to the bottom and he suddenly realized he was no longer wearing any clothes. Slowly the events of earlier that evening came back to him, and he realized where he was: Dwight’s barn.  
“DWIGHT!” Jim yelled! “DWIGHT! Hello! Is anyone there!”  
Silently Dwight checked both of the cameras that he had set up in the barn, he wouldn’t want to forget nay detail of tonight. Once sure that they both had good angles on Jim’s deliciously naked back side, he approached Jim from behind, smiling when Jim jumped at the feeling of Dwight’s hands on his naked back.  
“Don’t speak Jim,” Dwight started. “You’ll just make me mad and trust me you don’t want to be punished.” Dwight emphasized his last point with a quick slap on Jim’s back. “From now on, I’m your master. I’ll use you whenever I want to, and I’ll let whoever I want to use you. You will refer to me as Dwight when we are at work, but as Daddy at any other time. I will use your body for my pleasure and if you break my rules, I will punish you until you break,” Dwight added the last in a dark whisper into Jim’s ear.  
“What! Dwight, I think you’ve finally cracked, let me go! If you let me go now, we can just pretend this never happened-“ A sharp smack on Jim’s left ass cheek cut off the rest of what he was going to say. The one was followed by four more, all harder than the last, in the exact same place.  
“I said call me Daddy. I’m going to have a lot of fun punishing you Jim, turning you into my perfect slave,” Dwight’s fingers began to explore Jim’s body, squeezing his small backside, kneeding the lobes of his ass. “You should’ve read your contract more closely Jim, it’s all right there in black and white, with your legally binding signature at the bottom.”  
Jim had heard enough, he began struggling with all of his might, managing to break one of the ropes binding his ankles. He swung that leg back at Dwight, managing to nail him in the kneecap, knocking him over. But in no time, Jim felt a new pair of hands on him, restraining his leg once again.  
“Thank you Mose,” Dwight groaned, stretching out his injured leg. “Jim, Jim, Jim, I don’t think you understand. You signed a contract I had drawn up by an actual lawyer. It’s legally binding and if you break it, not only will you likely go to jail, I’ll send Pam and everyone in the office a copy along with some of the photos I took of you while you were out cold. It’s over Jim. Now act like a good little boy, and behave.”  
Jim was speechless.  
“Now I think you’ve earned yourself a punishment tonight,” Dwight said, standing up. He pulled a dirty cloth out of his pocket and stuffed it in Jim’s mouth. He walked over to the side of the stable and picked up a thin piece of wood. “You won’t enjoy this Jim, but I will.”  
Blows from the cane started raining down along Jim’s butt and upper thighs, not giving enough time between hits to recover from the pain of the last one. After 10, Dwight pulled the rag out of Jim’s mouth.  
“What do you call me?” Dwight demanded.  
“You’re crazy,” Jim panted.  
Another 5 blows rained down on Jim, “What do you call me?” Dwight demanded again. Jim was silent.  
After another 5, Dwight repeated himself once more, “What do you call me?”  
“…Daddy…” Jim said quietly. Dwight smiled, this was going better than even he’d thought it would.  
“That’s right, and Daddy’s going to make it all feel better now.” Dwight cooed as if talking to an actual infant.   
Jim couldn’t believe the situation he was in. He wanted to just close his eyes and pretend this wasn’t happening but the sound of a cap snapping open made his eyes go wide once again.  
“Dwight, what was that! Dwight just stop, this can all be over…”  
Dwight held the bottle of lube he had pulled from his pocket, smearing a generous amount onto two of his fingers. ‘Don’t want to break my new toy’ he thought to himself ‘at least not yet’. Snapping the bottle closed, he tossed it to the ground and unceremoniously shoved his two greased fingers up Jim’s unprotected virgin anus. The broken sound that Jim made was a mix between a gasp and a scream and his entire body jerked away from the unfamiliar intrusion. But the was no give in the ropes binding Jim to the barrel, forcing his body to take all that Dwight wanted to give him.  
“That’s not what you call me,” Dwight whispered in Jim’s ear, leaning against the taller man’s bare back.  
“Daddy…” Jim gasped out. “Daddy please stop, just stop...please,” he begged.  
Dwight groaned in pleasure at hearing those words come out of Jim’s mouth. Straightening once more, he began to roughly thrust his fingers into Jim’s hole, eliciting the sweetest sounds of pain and pleasure when he would rub against Jim’s prostate. As Dwight added a third finger, he began a torturous rhythm against Jim’s prostate and soon Jim’s long member was hanging stiff against the side of the barrel, his large balls swelling painfully as he leaked pre-cum onto the barn floor. Jim began to thrust slowly into the barrel, searching for relief against the rough wood grain. Dwight kept up his assault on his prostate until Jim’s small moans alerted him that he was on the verge of orgasm, then he cruelly withdrew his fingers and walked around to where Jim’s head was hanging limp against the barrel.  
“Nooo,” Jim moaned, his empty asshole trying to close around something, anything to keep up that delicious friction against his prostate. He had been on the verge of the most intense orgasm of his life, he couldn’t even see straight.  
“Shh, my little whore,” Dwight smirked. “You’ll come when I say that you can come. Now is the time for listening, so I’m going to gag that pretty mouth of yours,” Dwight shoved the dirty rag back in Jim’s mouth. “I can’t wait to have those pretty lips on my cock… but that can wait for now. I have five rules Jim. Five rules that you will now be living your life by. The first one, you already know, you will always refer to me as Daddy at any point we aren’t at work or when we’re alone. Second, you will only come when I expressly give you permission to. Third, you will pleasure me and whoever I choose, whenever and wherever I choose. Usually that will just be me and Mose of course”.  
Mose giggled from somewhere behind Jim, reminding him of his presence. Jim felt his face go red, he had forgotten that Mose was here and had witnessed this humiliation.  
“But of course I plan on using your services to close deals with large clients or entertain my friends when we have parties. Fourth, from now on you must always keep yourself ready for me at any time, so you have to keep yourself properly lubed at all times, no matter where you are. And fifth, you can’t have sex with Pam unless you ask me first. Your body belongs to me now. Break any of these rules and I will punish you and the punishment won’t always be as tame as those cane lashings you just got. I’ve been recording tonight, as I likely will most nights, for my personal enjoyment, and I won’t hesitate to send them to everyone in the office I need to get you to get in line Jim.” Dwight paused to look into Jim’s eyes, pulling out the gag. “Now would you like to come?”  
“…Yes, Dwight” Jim said, but realized his mistake almost immediately when Dwight’s eyes got dark. “I’m sorry! I mean yes Daddy! Daddy!” Jim cried out but Dwight had already walked behind him and picked up the cane once more. Jim heard the swish through the air before the first lash landed, on his upper left thigh. Jim hung his head and sobbed at the pain.  
“You’re going to get ten more. After each one, I want you to tell me how many that was, then thank me for giving it to you. If you scream, we’ll start over,” Dwight commanded, bringing the cane down once more.  
“One, thank you Daddy,” Jim said in a voice he hardly recognized as his own. Another lash on his poor abused ass cheeks. “Two, thank you daddy,” but on the third lash Jim couldn’t help but cry out. As soon as he could quiet himself, Dwight hit him with the cane again. “One, thank you daddy,” Jim said, tears in his eyes and running down his face.  
More lashes rained down on Jim until finally, “Ten, thank you Daddy.” Jim’s body went visibly limp, everything except his rock hard cock hanging between his legs. He knew it was wrong but the pain only seemed to make him harder and he was now so desperate to cum he knew a single stroke could probably set him off. Behind him, Dwight still hadn’t put down the cane.  
As Dwight watched Jim’s naked back rise and fall, he lifted the cane again, but this time not to strike. He prodded the rounded end of the cane against Jim’s swollen asshole, teasing. This elicited a small groan from the bound man. Smiling, Dwight pressed harder, thrusting the first few inches of the cane into Jim, angling the wood so that it just barely brushed against Jim’s engorged, over-sensitive prostate. Withdrawing it, he quickly thrusted it back in and further than the first time. Though the cane was thin, he wanted to start training Jim to accept long packages, his own was more than generous. Back and forth he worked the wood, brushing against Jim’s love button until Jim couldn’t stand it anymore and came all over the sides of his legs.  
Jim’s orgasm was so intense, he thought that he’d blacked out for a moment. It was as if a river of cum was gushing from his body. His orgasms had never been this intense with Pam. ‘No don’t think that’ he chastised himself, ‘Pam is your wife and you love her’. But he had to admit, in the dark corners of his mind, this was the best he’d ever had and on some level, he wanted Dwight, wanted him to punish him, to fuck him hard.  
Dwight smirked at the shaking salesman. ‘Oh how the mighty have fallen’ he thought to himself. Walking over to where one of the cameras was mounted, he zoomed in on Jim’s quivering asshole then on his softening cock and the mess that it had made.  
“I don’t remember telling you that you could come,” Dwight said, approaching Jim once more, and jerking Jim from his post-orgasm haze. A sense of dread began to rise in Jim’s stomach, he didn’t think he could take any more cane lashes.  
Once Dwight stood directly in front of Jim, he commanded him, “Lower your head”. Jim did as he was told, lowering his head until his chin pressed into the side of the barrel and he could only see Dwight’s shoes. ‘He’s still dressed from work’ Jim realized. ‘I’m here naked and spread to the world and Dwight looks like he’s at a business meeting’. The sound of a zipper quickly pulled Jim back to the reality of his current situation. A firm hand kept Jim’s head down, while Jim began to feel a warm sensation on the back of his head and neck.  
“You know this is how animals claim each other in the wild. Now I really am telling all the world that you’re my bitch and everyone will know whose property you are,” Dwight mocked Jim as he emptied his bladder on the back of Jim’s head. Once he finished marking his property, he tucked himself back into his pants. He wanted to try out his new toy so badly, but tonight wasn’t the night for that. But tomorrow…  
Leaning down to loosen the ropes around Jim’s arms, Dwight spoke to Jim again. “Go home and clean yourself up. Be at work on time tomorrow and don’t forget my rules. I think we’ll be having a lot of fun tomorrow, in my new office.”  
And with that, Dwight and Mose walked out of the barn together, leaving a dazed Jim to find his clothes and keys in the corner of the barn. Jim noticed the clothes were the same ones he’s arrived in. except his boxers had been switched for a skimpy green lace thong. The fabric felt too rough against his used asshole, but he slid them on anyway, every step afterwards sending a shot of pain and arousal through his body.


	3. Chapter 3

**Summary for the Chapter:**

> Dwight/Jim in the office

The drive to work the next morning was the most suspenseful 20 minutes of Jim’s life. This morning had already been awkward, having to dodge Pam’s questions about why he’d been out so late and why he wouldn’t even give her a kiss before jumping in the shower. Now, as Pam chatted away in the passenger seat, his stomach was dropping lower and lower with anticipation every mile they got closer to the office.

“Jim, are you listening?” Pam asked. “Yeah, I think you’re right,” Jim said hastily, trying to cover for his lapse in attention. “So you want to have Dwight over for dinner next week? To thank him for letting you stay on?” Pam clarified. His body went numb.

“No! I-I just mean that’s not really necessary, you know? I don’t think Dwight really cares about being thanked or anything.” Jim didn’t want to think about Dwight being in his house, talking to Pam, seeing their bedroom… But for some reason as soon as the idea of Dwight in his bedroom entered his brain, he couldn’t get it out. He was helpless to just sit there and image the other man, pressing him down into the bed, unbuttoning his shirt, stroking him until he was hard…. It wasn’t until the sharp snap of Pam’s door closing jerked Jim out of his fantasy that he realized he was sitting in the Dunder Mifflin parking lot, gripping the steering wheel with white-knuckled hands. Shaking himself, he slowly got out of the car and he and Pam made their way up to their office.

Bracing himself, Jim turned the corner, but Dwight’s office had all of the blinds closed and Dwight himself was nowhere to be seen. Relaxing just a bit, Jim took his seat and began opening some of his new emails. The first hour of work went by calmly, Jim answered a few calls, landed a new client, and discussed the upcoming Phillies game with Darryl.

“Conference room meeting, 5 minutes,” Dwight’s voice suddenly sounded from behind Jim, causing him to nearly jump out of his skin. As all of his coworkers made their way into the conference room, Jim purposely chose a seat towards the back, along the wall so that he wouldn’t have to look at Dwight straight on. And as Dwight talked about sales reports and monthly quotas and growth percentages, he found he couldn’t focus on anything except how often Dwight seemed to look at him. Was it normal for Dwight to look at him for that long? Was he smirking, could anyone else tell? Does anyone else know something is different? It was a relief when the meeting was finally called to a halt, 40 minutes later.

“Jim, I need to see you in my office,” Dwight called quietly to Jim as he tried to skirt out of the room. “It’s about a special project I need you on, it will take a while to discuss all the details,” Jim’s body flooded with adrenaline. With one final look back at Pam, who gave him a smile and a thumbs up, he let Dwight lead him into the manager’s office, and close the door behind him. It was a surprise to Jim that the office looked as though it had recently been under construction, some wooden planks leaned against the corner, the dry wall looked fresh and there was a small amount of wood shavings on the carpet. A number of power tools sat on the window ledge.

“Down,” Dwight said, not giving Jim a single look of acknowledgement, as he crossed to the other side of the large wooden desk that still occupied the office. Jim sank into one of the chairs on his side, trying to make himself look as small as possible.

“No, not sit you idiot, I said down,” Dwight ordered again. Jim slid out of the chair to his knees. “That’s better, now come around here,” Jim shuffled around to the other side of the desk, where Dwight leaned back in his chair, obviously enjoying this situation. “I’ve had some work done to this room in the past few days. I tripled the insulation in the walls, making them practically sound proof. I had this done so that I could listen to my Metallica loudly without anyone complaining, but it works perfectly for our little arrangement, so I can use you all day and no one will even know.” Dwight began unbuckling his belt, and unfastening his pants. He pulled out his limp dick and let it sit on his trousers. He wove the fingers of his left hand into Jim’s hair, pulling Jim’s head down so that his face was only an inch from this flaccid penis. The size was intimidating to Jim, even soft the member had to be at least 6 inches.

“Open your mouth,” Dwight whispered. Part of Jim’s mind wanted to resist, to bite down, but that part of his mind was currently being overthrown by the part that was so turned on by all of this dominance and kinkiness it was screaming for Jim to obey. Slowly, Jim opened his mouth. Dwight wasted no time, using his right hand to guide the soft dick into Jim’s mouth.

“There that’s perfect, I knew you had good cock sucking lips,” Dwight said smiling down at the other salesman. “Just hold it there for now, taste how good Daddy’s dick is for you,”. The 15 minutes were spent like that, with Jim obediently sitting on his now asleep knees, holding Dwight’s slowly hardening penis in his mouth. Jim wanted to cry from the humiliation, of sitting here being watched by Dwight like this. All Jim could taste was the salt on Dwight’s skin, all he could smell was Dwight’s musk, with Jim’s nose shoved into his pubic hair as it was.

“Start,” is all that Dwight said, leaning back further in his chair. Jim had never sucked a dick before, not even in college, but he’d seen enough porn to start trying. He ran his tongue over the bulbous head, tasting something salty that he didn’t want to think about. His jaw was already killing him from the past 15 minutes, but Jim pushed through the pain, bobbing his head back and forth, like Pam had done on the few occasions that she’d consented to blow him. It was difficult because, while Jim had always considered his dick to be above average, he couldn’t even fit half of Dwight’s cock in his mouth at once. The hand in Jim’s hair suddenly tightened, forcing Jim’s head down even further. Jim gagged when Dwight’s large member hit the back of his throat, and Dwight let out a small groan. Between the hand in his hair guiding him up and down, and Jim’s sloppy licks and slurps, it was still another 10 minutes before Dwight came with a small shout. The first hot jet of cum took Jim by surprise, it wasn’t the worst taste he’s ever tasted, hot and salty and masculine, but it was by no means pleasant. The next jet came before Jim had even had time to fully process the first one, and then next came soon after that. Finally it seemed that Dwight was done cumming. Jim tried to pull his aching head back, but he was held firmly in place by Dwight’s hand. Jim felt Dwight’s cock slowly soften and shorten before he was allowed to pull away.

“I didn’t even have to train you to swallow, good slave.” Dwight praised. “And what do you say to me?” “…thank you Daddy,” Jim guessed. “Good boy. Now stand and strip.” Jim stood slowly, he was afraid is numb legs might give out on him. He began taking off his clothes, in a mechanical sort of way, hoping if he had an all-business attitude, it wouldn’t feel as dirty or naughty. But with Dwight’s hungry eyes on every inch of exposed skin, Jim could feel the blood rush into his cheeks, and rush into …. Other places. Once he worked his boxer off over his half-hard dick, he looked back to Dwight.

“Oh you dirty slave, you’re enjoying this. Are you hot for Daddy? Do you want Daddy to fill you up and let you cum on his big cock?” At Dwight’s hot words, Jim’s dick stiffened further. Dwight suddenly stood up, pushing Jim down over the wooden desk. Jim heard a drawer open and close and a lid snap open. His eyes were fixed on the window in front of him, where, behind the drawn blinds, his wife along with a dozen other people were sitting and working, with no idea of what was going on less than 5 yards from them. The kinkiness of this situation was getting Jim so hard, shocking the mild-mannered part of him who had never done anything wild before. A lubed finger pressed against Jim’s anus, which still hadn’t fully recovered from its rough use last night. Dwight moved his finger in an out, in and out, then added two more at once. Jim felt like he was going to tear open, but when Dwight hit his prostate, Jim nearly came at once. Slowly he was stretched by the fingers inside of him.

“You know, one of your rules is that you’re supposed to do this yourself. You’re supposed to keep yourself ready for me at a moment’s notice,” Dwight’s soft words started a panic in Jim’s stomach. “I have to punish you, but not now. Come directly to Schrute farms after work, I’ll punish you there. For now, I think I’m ready to try my new toy.” Dwight shifted behind Jim, and started pressing his full 9 inches into Jim. The sounds that Jim was making threatened to send Dwight over the edge right then and there, but he was determined to make Jim cum first, on only his cock. Once he’d fully seated himself within Jim, he started up a slow thrusting pace. Jim was so tight, his inner walls gripping Dwight’s hard cock so perfectly, it felt like a glove. As Dwight thrust back and forth, he began increasing his speed, jackhammering into Jim’s sensitive hole. Every time he was engulfed by Jim’s hot ass, Dwight’s eyes rolled back in his head. Pumping his hard cock in and out, he felt Jim’s inner walls contract around him, gripping at him.

Dwight’s brutal pace made his dick hit Jim’s prostate almost every thrust, driving Jim crazy. Jim could already feel his stiff cock leaking pre-cum onto the floor, but none of that mattered, the only thing that mattered was Dwight and his burning hot, hard as steel rod pumping in and out of him. On an especially brutal thrust, Jim felt himself go over the edge. He barely stopped himself from screaming, as black dots danced in his eyes and his dick spit out more cum than ever.

Dwight felt Jim’s orgasm through his muscles, his hot little channel milking his hard dick, and Dwight came with one last thrust, one hand gripping Jim’s hair, pulling him back even further on his cock, shooting his hot seed deep into Jim. For a moment, neither man spoke, the only sound was panting. Dwight pulled out and sat back in his manager’s chair.

“Jim, I’m very disappointed in you.” Jim’s stomach dropped. “You’ve just broken your second rule of the day. I have to say, I’m not surprised, but I am upset. Now clean me up, and clean up this disgusting mess you made on the floor _without permission_ , while I think of what I should do to you.” Jim was quiet as he slowly lowered himself to his knees once more and licked at Dwight’s softening cock, grimacing at the combined taste of the lube, Dwight’s cum, and his own anal juices. He then leaned down and licked his own cum off of the floor as best he could. A sudden intrusion in his over-stimulated backside made him cry out. Dwight inserted one finger back into Jim’s hole.

“I didn’t like the way it looked, so empty, just begging to be filled…. You know what, I’ve decided your first punishment. You’re going to keep something of my choosing in here all day, until I see you at Schrute farms tonight for your second punishment. Oh don’t look at me like that Jim, I know that you want it. This is barely even a punishment, you should be happy at how merciful I’m being.” Dwight looked around the office until his eyes settled on something, a thick, shiny, yellow highlighter. Grabbing up the highlighter, he pushed it into Jim’s stretched out asshole. Jim yelped at the cold plastic.

“Thank you Daddy” Jim grated out.

“I know it’s not anywhere as big as me, but it’ll keep you aroused all day, and thinking of how good it felt to have Daddy’s big juicy cock inside of you. Get dressed.”

A few minutes later, with a final swat to Jim’s backside, making him squirm as the highlighter wiggled inside him, brushing too close to his prostate, Dwight opened the door for the now dressed Jim. “Good work Jim, we’ll continue this discussion tomorrow,” Dwight called loudly, as Jim took his seat at his own desk, every small motion causing a wave of sensation in his ass.


	4. Chapter 4

**Summary for the Chapter:**

> Jim meets Dwight at Schrute farms and gets more than he expected

By the end of the work day, Jim was about to burst. The highlighter inside of him had kept him so aroused all day, brushing ever so slightly against his swollen prostate, it was a wonder that he hadn’t blown a load already. A few times already he’d been so close to coming, he found himself subtly rocking in his chair, searching for that delicious friction, rutting his leaking hard-on into the cushioned bottom of his office chair. Thank goodness he’d had extra clothes in his car for work outs, because Jim had ended up running down to get extra clean underwear after his pre-cum had soaked through the pair that he was wearing. Multiple times throughout the day, Jim looked up to see Dwight watching him with carnal hunger in his eyes and every time, Jim would feel himself slide dangerously close to creaming in his pants like a 15 year old. Something about Dwight watching him, when he knew how aroused he was, but unable to do anything about it… it kept Jim squirming in his seat long after Dwight had left the room.

Now, as Jim sat there, watching the time tick by, counting down the minutes until he would hopefully be allowed to cum again, he felt his impossibly hard cock harden further as he thought about what awaited him tonight at Schrute farms.

After what seemed to be the longest work day of his entire career, it was 5 pm. Jim immediately sprang out of his seat, and grabbed his coat.

“Woah, slow down Jim,” Pam called, logging off of her computer slowly and beginning to gather her things. Jim smiled, but he internally pleaded for Pam to hurry because he didn’t know how much longer he could last. Standing up with the highlighter wedged firmly inside of his ass was a completely different sensation that sitting down, the marker seemed to slide higher, if possible, stimulating Jim even further.

“Goodnight, everyone!” Pam called as Jim impatiently led her from the office. Once they’d settled in the car, Jim peeled out of the parking lot.

“What’s gotten into you? You’ve been acting weird all day? Are you sick?” Pam asked, suspicious.

“Yes! I-I mean yes, I’m really sick. I forgot to tell you but I made a doctor’s appointment during lunch for tonight. In a couple minutes actually, I’m not sure when it will be over…” Jim trailed off.

“Oh you poor thing, I should’ve known, you’ve been so flushed all day,” Pam continued to say things that Jim never heard because at that moment, the car hit a pothole and the little improvised butt-like inside of Jim did something wicked to him. Jim was helpless to do anything other than continue to point the car straight as his body, which had been so wracked with arousal all day, came, right there in the car.

Jim’s prostate pulsed against the unyielding plastic of the highlighter, giving him just enough of that amazing texture sensation to cum. His dick exploded, with a force that shocked even him as it shot its load into Jim’s pants. Pleasure made his head swim, it was like ten orgasms at once.

“Jim? You’re crying. What’s going on?” Pam said, oblivious to the sexual experience her husband had just had.

“I just think I’m really sick, my stomach hurts, I really need to get to the doctor,” Jim gasped out, still quaking with aftershocks, amplified every time they hit even the slightest bump in the road.

“Oh sweetheart, you should just heard straight to the doctor’s, don’t even bother coming inside to change out of your work clothes, I don’t want you to be late.” Pam leaned over to kiss Jim’s cheek as they pulled into their drive way. Sliding out of the car, she waved from the front lawn as Jim quickly backed out again.

Now that he’d cum, their anxious adrenaline-fueled thrill he’d been feeling about tonight turned to something more akin to dread. Dwight was sure to have something awful planned for him. For a crazy moment, as Jim got on the main road to take him to Schrute farms, he thought about turning around, and going home. But as awful Dwight was going to be to him tonight, he couldn’t imagine the trouble he would be in if he didn’t show up. Besides, a small part of Jim had to admit, he was really starting to enjoy being punished by Dwight…

Pulling up to the farm house, Jim put the car in park, and before he had time to second-guess himself, walked up to the door and knocked. To Jim’s surprise, it wasn’t Dwight who answered the door, but Angela. Jim knew Dwight and Angela had been dating on and off for a while, but he never expected to see her here, at least not right now.

“He’s waiting for you inside…….slut,” Angela said to Jim, looking down at him with her nose upturned, moving aside so that Jim could slide by her in the narrow entry hall. Jim’s mind was reeling. Did Angela know? How much did she know? Would she keep this a secret?

As Jim entered the main room, his mind instantly noted a few things. First, there were several cameras set up in the room, in each of the four corners, all focused on one area in the center of the room, where a wooden bench was. Second, near the bench was a table with an assortment of different instruments that Jim hoped to god were meant to intimidate him and not to actually be used on him. Lastly, Dwight was sitting on the couch, completely naked, drinking a beer, and he wasn’t alone. Mose sat next to Dwight, equally as naked.

“Strip.”

The single word sent shock waves through Jim, but he forced his frozen muscles to move. Angela entered the room behind him and walked over to sit on the arm of the sofa, next to Dwight. As Jim’s shirt fell to the floor, we wasn’t sure what was worse, the possessive, hungry look he was getting from Dwight, the judgmental look he was getting from Angela or the way that Mose couldn’t seem to stop giggling. With a deep breath, Jim unbuckled and slid down his pants and boxer-briefs at once, revealing the sticky mess of his cum and pre-cum. He waited.

“Jim, Daddy is very disappointed in you. This was supposed to be a punishment, but you obviously enjoyed yourself way too much to have learned any kind of lesson. You did not have my permission to come,” Dwight stood and began to walk toward the naked man. It took every ounce of self-control for Jim to not back up and cower.

“Lay on your back,” Dwight whispered softly, but there was hint of danger in his voice. Jim did as he was told, backing into the bench, and laying down. It was just the right size so that Jim’s feet could barely brush the ground, with his head hanging off the other side.

“Mose,” Dwight said, and the two men began fastening Jim’s long legs with rope to the bottom corners of the bench. Next were Jim’s arms.

Angela stood then, walking around to join the two men as they stood just in front of the bench, appraising Jim’s body.

“Now Jim, you understand the way this works. You do something bad, Daddy has to punish you. How else will you learn?”

“The bible says that slaves should obey their masters,” Angela chimed in.

Dwight reached forward, his long fingers deftly entering Jim’s asshole to extract the highlighter. Jim couldn’t help the moan that escaped from his lips.

“I was nice, slave. As your punishment, I allowed you to be aroused all day, that’s a gift. I only asked in return that you respect me as your master and wait to cum until you were here. But you couldn’t do that simple thing!” Walking around to Jim’s head, Dwight commanded, “Open.”

Jim obeyed, and found the highlighter jammed into his mouth. “Suck on this, clean it for me, imagine that it is my cock,” Jim choked at the taste but didn’t dare spit it out, instead he held the repulsive object in his mouth, trying not to touch it with his tongue. “I think you need to learn a lesson tonight Jim.”

Dwight walked over to his tools. Here he had laid out all the different things he planned on introducing Jim to tonight. He’s eyes scanned the contents, where should we start? His eyes landed on two sliver nipple clamps.

Grabbing the metal pieces, he reached across Jim’s chest and attached one to one of Jim’s nipples. The muffled squeal from Jim had blood rushing to Dwight’s crotch. As he attached the second clamp, he twisted the first and pulled. Jim bucked, but the rope held. Jim had nowhere to go. Dwight continued to twist and pull at the clamps, occasionally pulling one entirely off, and re-clipping it.

Jim was utterly confused by the pleasure/pain he was feeling. His nipples were on fire, but every tweak hardened is dick a little more. He really was sick, but he was so getting off on this. Too soon Dwight walked away, back to the others.

“Angela, you are our guest, why don’t you try the toy first.”

“Thank you Dwight, always the gentlemen. What can he do?” Angela asked, eyeing Jim’s bound form.

“He can do whatever you want him too,”

Smiling, Angela walked around the bench to Jim’s head. She snatched the highlighter out of his mouth. “Is this really what you call clean? This is still disgusting. Can you lick anything properly? I guess we’ll find out.” Angela pushed her skirt and granny panties down, revealing quite a large amount of pubic hair, stepping out of them so that she was naked from the waist down. With one large step, she swung one leg over Jim’s face, which hung perfectly at waist height.

“Lick it, like a cat,” Angela yelled. Jim stuck his tongue out and began to lick tentatively. Pam made him go down on her a lot, she was quite bossy in bed, often only letting him touch her at all if he would eat her out first. But being straddle while his head hung upside down was a new experience for him, and took several test licks, before he found Angela’s lips. He thrust his tongue in every direction, circling her clit, sucking the hard nub into his mouth.

Arousal coursed through Angela’s body at full speed. The feeling of Jim’s mouth beneath her was so amazing. Angela found herself to be horny almost all of the time, but her strict upbringing and rigorous morals didn’t allow her to take enough lovers or act promiscuously enough to satisfy her urges. But here was someone, a slave, who’s only purpose was to serve other’s sexual needs. It didn’t matter what he thought of her, because he didn’t matter. He would never tell anyone, he was just a toy to be used hard and put away wet. Just the idea had her cunt wet. As Jim stabbed his tongue up into her vagina, impaling her on his warm slick flesh, she ground down against him, rutting into his face.

Beneath her, Jim was eating his heart out. With his nose wedged into Angela’s ass and his mouth full of Angela’s pussy juices, it was getting a little harder to breath. This needed to end soon, so he redoubled his efforts, blowing on Angela’s clit, then circling it with his tongue.

“That’s it, ride that sow girl, ride it,” Dwight whispered, leaning down over Jim’s body to kiss Angela, his hand pulling at one of her nipples. Angela cried out, she was so close to coming she could feel it. Jim adjusted beneath her, ducking his head to push in nose up into Angela’s cunt, while simultaneously biting gently on his swollen clit. Angela exploded, flooding Jim’s face with her juices, jerking violently a few times, before collapsing forward onto Jim’s chest.

After a few moments, Angela, pushed herself off of Jim. “That is a very good toy that you have Dwight,”

“I’m glad that it was to your liking. Mose why don’t you go next, you are the only one here who hasn’t gotten to try our toy.”

Mose walked forward eagerly. Jim couldn’t see, but Mose was sporting an erection slightly shorter than Dwight’s, but almost twice as thick. Laying one hand on each of Jim’s thighs, Mose leaned forward to push into Jim.

Jim supposed he should’ve become accustomed to large object entering his rectum by this point, but Mose’s huge rod made Jim cry out so forcefully, Dwight broke off from Angela, with whom he’d been passionately making out. Picking up Jim’s soiled, cum soaked underwear, he walked around to Jim’s head.

“Baby, it’s really better for slaves to be seen and not heard, at least until we want to hear you.” Dwight said, shoving the cotton into Jim’s mouth. “You know this is Mose’s first time with a person,” Dwight whispered in Jim’s ear, as Mose continued working his monster shaft inside of him, inch by inch. “Sure, he used to fuck this old scarecrow out on the east field, and I’ve caught him with animals on a couple of occasions, but you’re his first real person. So make it good for him Ok?” Dwight retreated, grabbing Angela, and taking her mouth forcefully once again.

Mose finally seated his entire cock inside of Jim, and every nerve ending inside of Jim was alive. Mose was too big to miss his prostate so every brutal thrust nailed him right in his pleasure center. Within minutes, Jim was drooling through the makeshift gag, as Mose hammered into his ass. His long cock was hard and hot, Jim felt that we would forever be branded by the iron-hard length. How could he go back to regular sex with women after the way that he was feeling right now?

Mose started to speed up as he approached his climax, his nails biting into Jim’s thighs. Dwight & Angela’s cries from the corner alerted them that the other pair had just finished as well. Jim was so close, he could feel his orgasm rising up inside of him, so close, so close…

One last thrust from Mose, and Jim could feel Mose’s hot cum shooting deep inside of him, to his very core. Load after load sprayed inside of him, and Jim’s eyes rolled back in his head, he felt himself start to go over the edge- A hard grip clamped down on his cock, stopping his orgasm. Crying out, Jim tried to thrust into the hand, but the grip was steel. Opening his eyes, he saw Dwight’s hand wrapped around his hard dick. Sexual frustration was a palpable force inside of Jim. He’d been so close… He cried out through his gag, as his dick throbbed, needing release desperately.

“I didn’t give you permission.”

Dwight walked back to the table, selecting what looked to be a taser. Seeing this, Jim immediately started to protest from under his gag.

“Calm down you infant, it isn’t enough voltage to do any damage really, just to have some fun.” Dwight walked towards Jim’s lower body. “Despite how scared I know you are right now, your cock is as hard as ever. I think you like the pain Jim, I think you’re a dirty little pain slut and you just need to be reminded of that. But don’t worry, I’ll be reminding you of that multiple times a day from now on.”

Grabbing Jim’s balls roughly, Dwight held up the taser to Jim’s sensitive perineum and let out a shock. Jim’s scream was muffled by his dirty underwear. Dwight applied a few more shocks, until Jim’s hard on eventually began to wane. Smiling at Jim’s softening penis, Dwight tossed away the taser, and pulled another instrument out from behind his back. It was a long silver metal rod with a bulbous head the size of a marble and several other smaller bumps along it.

“This is called a sound, Jim. I think you’re going to like this a lot,”

Dwight pinched the tip of Jim’s penis, opening the slit wider. He slowly slid the sound down inside Jim’s cock, forcing the first bulge past with a pop. It was like nothing Jim had ever felt before. As the large head made I’s way further down, towards the base of Jim’s cock, the pressure became intense, but when Dwight withdrew the sound, the head making a pop as it exited Jim’s penis, a wave of pleasure overtook him. Up and down, in and out, Dwight worked the cold metal sound, fucking him with it. Jim felt so feminine, having his slit fucked open with this long metallic phallus. The sensation was making him hard again, making it more difficult for Dwight to work the sound in and out of him. Jim was in a frenzy, he needed to cum so badly, he couldn’t stand it. The pressure in his balls felt like they were going to explode. His hips began moving of their own accord, thrusting up and down, desperately trying to fuck himself on the artificial penis inside of him. Eventually, Dwight tossed away the rod, and reached to remove the soaked wad of Jim’s underwear from his mouth.

“Do you want to cum?”

“Yes, please Daddy.”

“Beg me,”

“Please, please Daddy, please let me come Daddy, please, I’ll do anything,” If Jim hadn’t been so out of his mind with lust, he would’ve been taken aback by the words coming out of his mouth.

Dwight’s hand wrapped around Jim’s cock, giving one strong stroke. “No,” Dwight said. “You may not come.”

Angela’s hand reached forward, cupping Jim’s balls, massaging them in her delicate hands as Dwight pumped his fist up and down Jim’s stiff dick again. Jim cried out as a bead of pre-cum appeared on his tip.

“Please, Daddy Please,”

“No,” Dwight said again.

Mose’s hand now circled the Jim’s head, his thumb rubbing across his slit, collecting that drop of pre-cum to use as a lubricant as he continued rubbing his fingers in a circle around Jim’s cock. Dwight gave another pump of his fist. Jim had already been on the edge before, now his dick was so overwhelmed by sensation he could feel his orgasm rising up once again.

“PleaseDaddy, PleasePleasePleasePlease, I need to cum so bad please please please,” Jim let this begging spill forth, not even forming coherent sentences.

“You belong to me,”

“I belong to you Daddy!”

“Now cum,” Dwight commanded, pumping his fist up and down Jim’s cock with wild abandon as Jim’s orgasm overtook him. As many times as he’d already cum today, he wouldn’t have thought that his dick was still capable to the intensity of orgasm that he experienced. His load landed on his stomach, painting him white under all of his cum. Waves of pleasure spiraled through his body, out of control, and Jim wept under their intensity. It went on so long, Jim wasn’t sure if he would ever stop.

Aftershocks were still rippling through his body as Mose untied his legs and Dwight forced him up, half supporting him after Jim’s weak legs gave out on him. Dwight walked him to the door and handed him back his pants.

“Go home Jim, I’ll see you bright and early tomorrow morning.”


	5. Chapter 5

Jim sat in his office chair, chatting absent mindedly with his wife. The morning had come and gone with no sign of Dwight, and now it was 3pm. Though he knew it was unlikely, Jim began to believe he might get through a whole day without Dwight’s… demands. But he should’ve known not to tease himself with an impossible hope.

“Jim can I see you in my office?” Dwight called out, standing several feet behind Jim, in the door way to the manager’s personal office. The usual chill ran down Jim’s spine.

“You’ve been spending a lot of time with Dwight on your special project, do you think it’ll be ready soon?” Pam whispered to Jim as he straightened, standing up.

“Um, I don’t really know, it, um, it keeps sort of changing direction… we’ll see,” Jim stammered.

Turning around, Jim forced his feet to carry him away from his wife and towards Dwight. Dwight remained standing in the doorway, forcing Jim to shimmy past him sideways, eliciting a small shiver from the taller man when his sensitive nipples brushed Dwight’s shoulder.

“Angela, why don’t you join us too,” Jim heard Dwight say, immediately stiffening. Dealing with Dwight’s demands was enough without having to please multiple people. Behind him, he heard Angela enter the room and the door snap closed. Angela and Dwight sat down on opposite sides of the desk, but Jim remained standing.

“Strip.” Dwight commanded, not even deigning to look at Jim as he started unbuttoning his shirt. Slowly removing his shirt, followed by his pants and underwear and finally his shoes and socks, Jim stood there, his flaccid member swaying between his long legs.

Turning his attention back to the naked man standing before him, Dwight looked Jim up and down, appraising.

“I hope you’ve kept yourself lubed up today, because I’m not in the mood to prep you,” Dwight stood, unbuckling his belt.

“Yes Daddy,” Jim whispered, his voice dry. He’d barely gotten anything done today, with his constant trips to the bathroom every half hour to keep himself slick and ready.

Dwight tilted his head, his eyes still on Jim. “Angela will you check for me?”

“Certainly Dwight.” Angela rose from her seat. “Bend over, hands on the desk,” She barked to Jim, maneuvering behind him. Jim did as he was told, leaning down to place his hands on the edge of the wooden desk.

“Spread your legs, hurry,” Angela snapped, tight lipped. She kicked Jim’s legs apart, forcing him to widen his stance. With one hand, she gripped his left butt check, pulling it way from the other, exposing his slicked up anus. Unceremoniously shoving a finger inside Jim, Angela cruelly wiggled it, causing Jim to gasp as his barely recovered asshole was stretched.

“Yes, he’s prepared for you Dwight,” Angela said, removing her finger with one last cruel flick, aimed right at Jim’s prostate.

“I’m glad to see you’re starting to learn, Jimmy boy.” Dwight walked around the desk. With one firm hand on Jim’s back, he pushed until Jim was lying flat on the wood, the side of his face pressing into the cool surface. It took Jim a moment before he realized that he was in the perfect position to see Dwight’s computer screen. It was obviously intentional as Jim realized the movie clip playing on the desktop was starring him, tied to a barrel in Dwight’s barn. ‘ _This is the video from the first night_ ’ Jim realized, watching himself being mercilessly spanked.

“I told you that I was filming that night. In fact I’ve been filming most of our encounters, I’ve even had a few small cameras permanently mounted in here, to capture our little adventures,” Jim felt Dwight line up his hard cock with his own hole, only having half a second’s notice before Dwight thrusted in, seating himself completely. Jim’s head swam, struggling to adjust to Dwight’s steel rod of a penis. Even as Jim’s ass screamed in raw protest, having been used brutally over the past couple days, the needy, desperate, submissive side of Jim had his toes curling with lust.

Pulling back out, Dwight slammed in with a force that had Jim biting his lip, squeezing his eyes closed as his heels momentary left the ground.

“Open your eyes baby. I want you to watch that video, watch yourself as I fuck you.” Dwight growled. Jim’s eye’s snapped open, fixing on the computer monitor, watching as, in the video, Dwight began to fuck him with the wooden rod he’d just been spanked with. The memory sent blood rushing south as Jim remembered the sensation, the first time he’d had his prostate specifically stimulated by a man, by Dwight. The memory, combined with Dwight’s dick rubbing against his love button in the present had his dick hardening in record time.

“I remember how tight you were that night, I could barely work the cane inside you. You’re still that tight, gripping my dick like you need it, like you can’t live without it,” Dwight withdrew completely, leaving Jim gasping, his eyes wide and watering. Just a moment later, Dwight shoved back in, somehow stretching Jim further than before. Impossibly, Dwight’s dick seemed to have doubled in girth, splitting Jim open. The friction against Jim’s prostate was setting him on fire, Dwight kept up a brutal pace, bucking into Jim. Suddenly something shifted, a change in timing. Dwight was withdrawing as something else was pushing in, then the mystery object withdrew as Dwight shoved his member back in.

“Do you like that Jim? Being fucked with two cocks? Yeah, you’re taking it like a champ, like a little whore.” Behind Jim, Dwight held a rubber dildo in his right hand, fucking Jim with it alongside his own cock. It was one of his greatest fantasies but Angela had downright refused to try it with Mose, and Dwight didn’t want anyone else fucking his woman. So he’d settled with trying it with Jim. The sensation was all he’d imagined that it would be, feeling another cock shove into Jim’s hole, the added friction sending him into a frenzy.

Jim’s glazed eyes were fixed on the computer screen, but his mind couldn’t comprehend anything other than the delicious pounding he was getting. His dick was reaching critical hardness, leaking thin clear/white precum onto the carpet. Dwight switched the tempo once again, thrusting his own dick and the fake dick at the same time. Watching Jim’s sweet pucker stretch to a breaking point was so erotic for Dwight, he felt himself reach the edge. With one last thrust, he buried himself in his slave, painting his insides with his cum.

Feeling Dwight’s hot ejaculation inside him was enough to push Jim over, his own dick jerking wildly, painting the carpet as well as his legs in thick cream.

Pulling out, both himself and the dildo, Dwight walked back to his chair. “Clean up,” he ordered, turning to his computer.

Jim kneeled, scooping up as much of his cum as he could, shoving the thick, ropey liquid into his mouth before he lowered himself to lick at the stains on the carpet. Angela moved to leave.

“Where are you going monkey?” Dwight asked, disappointment coloring his tone.

“I’ll be back, I just have to use the restroom.”

“Oh there’s no need to leave,” Dwight said, rising out of his chair. Walking around the desk once more, he grabbed a fist of Jim’s hair, forcing his head from the carpet.

“Flip over, on your elbows,” Dwight ordered, picking up one of the office chairs and placing it down on top of Jim, its legs on either side of his abdomen. On his back, raised up on his elbows, it put his chain approximately even with the edge of the seat.

“As I re-watched our first encounter, I remembered the first time I marked you slave. Not with my cum, but with my urine, the way animals do in the wild and I found myself wanting to do it again, to remind you who you belong to.”

Jim felt his stomach sink, ‘ _How can I explain being covered in urine at work?_ ’

Dwight held his hand out to Angela, leaning in to whisper in her ear. An evil grin broke out across Angela’s tight lips. She quickly moved around the chair, hauling up her long dress and shimmying out of her voluminous granny panties. Stepping over Jim, as if to straddle his head, she sat on the edge of the chair. Resigning himself, Jim prepared to eat Angela out, leaning forward to give a tentative lick to her hairy pussy. To his surprise, Dwight moved behind him, holding his head in place with an iron fist.

“Drink,”

Suddenly salty sour liquid filled Jim’s mouth. Choking, he swallowed out of shock, coughing into Angela’s cunt. The taste was disgusting, the smell made Jim want to gag, but as hard as he struggled, Dwight’s hold held him in place. To prevent the punishment that he knew would follow any disobedience, Jim steeled his resolve, swallowing again. A few more swallows and Angela’s stream began to weaken, then stop. When Dwight still wouldn’t release Jim’s head, he licked at Angela a few times, cleaning of the salty liquid from her folds.

“Good boy,” Dwight praised, stroking his fingers through Jim’s hair. “Now it’s my turn,”. Pushing Jim back into a laying position, Dwight slipped his now soft cock out of his still unbuckled trousers and positioned the tip between Jim’s lips. His large, sweaty, musky balls rested on Jim’s face, over his eyes, is pubic hair tickling Jim’s forehead. As Dwight’s stream hit the back of Jim’s throat, Jim once again fought his gag reflex, but he found that he didn’t mind Dwight’s urine as much, it was sweeter, reminding him of the taste of beets. He swallowed down Dwight’s juices, sucking on the tip of his cock like a straw.

When Dwight’s bladder was empty, he leaned back, observing the sight of his slave.

“You can go, but come to Schrute farms after work, Mose misses you and I have a few… ideas to try out,” Dwight smirked.

Angela and Dwight began to right their clothes, but Jim stood, remaining completely naked.

“What Jim? Are you looking for a round 2?”

“Daddy, I… I need to ask a favor,” Jim said, staring directly at his feet.

There was a pregnant pause. “Oh really?” “Pam wants to have sex tonight, Thursdays are always our sex night, because her mom watches the kids.” Jim still found himself unable to tear his eyes away from the carpet.

“How about this Jim, if you are a good boy tonight, not a single mistake, you can fuck Pam tonight. But remember Jim, you aren’t allowed to cum. So you have to record it so I can be sure that you didn’t cum without my express permission.”

“Yes Daddy,” Jim dressed hurriedly, trying to subtly smell his breath, to make sure the stench of urine wasn’t too apparent. As he hurried to his desk, he could feel his stomach jiggling, full of urine. It made him feel dirty and low but the twisted part of him loved it, and he felt his dick harden. He found himself taking larger steps, to increase the jiggling sensation he felt as Dwight and Angela's juices bounced around inside of him, marking him internally, deeper than anything else could. ' _As their property_ '


	6. Chapter 6

Stanley’s hurried movements and muttering alerted Jim to the fact that the day had come to an end. Looking over to Pam, he saw her sign out of her email and start gathering her things. Following her lead, they walked out of the office together, riding the elevator down with Toby and Kevin. The ride home was quiet, openly punctuated by Pam’s small complaints about traffic.

“Hey Sweetie, I’ll be home a little late tonight. Dwight wants me to go see a big client with him tonight, we’re taking him out to dinner.”

Pam looked surprised and Jim knew it was because today was Thursday, date night. Well date night was a bit generous, it usually just consisted of them opening a bottle of wine and having safe boring missionary sex in their bed, like any other married couple.

“Oh-Ok, just hurry, I’ll go ahead and open the wine,”

“I will sweetheart, I promise,” leaning over, Jim pressed a quick kiss to Pam’s cheek, breathing in the clean scent of their soap and her shampoo. He watched Pam unlock their door before backing out of the driveway and following the now familiar route to Schrute farms.

Pulling onto the long dirt drive, Jim felt a flurry of what could only be classified as arousal. The bumps of the car driving over gravel sent adrenaline racing through his body as he prepared for what was ahead. Parking the car, Jim approached the door and knocked.

Mose appeared to open the door, giggling uncontrollably at the sight of Jim. More concerning to Jim however was the prominent tent in the front of Mose’s trousers. Mose pulled the door wider, indicating Jim should enter. Shimmying past the smaller man, trying desperately not to brush his raging hard on, Jim walked into the house, taking a few steps towards the living room.

“Hello Slave,” Dwight said briskly, from the corner of the main room. “Don’t get comfortable, I thought we might go for a change of location today. But first, remove your clothing.”

“Yes Daddy,” the words came obediently before Jim even realized he was speaking. Mechanically he reached up to his button down, removing each article of clothing and laying them out on the couch next to him until, finally, he slid off his boxers, adding them to the growing pile.

“Now follow,” Dwight directed, turning to open a side door leading off of the main room, leading outside. Jim stepped through the door, wincing as the gravel was abrasive against his soft feet. Not wanting to fall behind of the brisk pace being set by Dwight, Jim tip toed and hopped over the gravel path. It became apparent that they were headed for the barn, the sight of which made Jim shudder, remembering his first night as Dwight’s slave. Dwight paused to swing open the old wooden door, then ushered Jim inside.

Inside was a wooden bench very similar to the one that Jim had become so acquainted with during his last visit to Schrute farms. He also saw that the video cameras from last time were present, fixed on the bench. This bench was higher than the last one and had several extra features. For one, it wasn’t level. One side was higher than the other, making it slanted. There was also an approximately 6 inch diameter hole cut in the surface a few inches from the edge of the higher side. The pegs were screwed into the legs on the higher side of the bench and had little straps with locks on them.

“Go,” Dwight said, with a cruel push, making Jim walk towards the strange bench. Dwight place a firm hand on Jim’s back, bending him over at waist level over the higher end of the bench. As he laid down, his soft cock fit perfectly through the hole cut in the surface, leaving it limp and dangling beneath the table. Jim’s head hung just off the lower end of the table, leaving him staring at the hay strewn floor. Gripping Jim’s calves, Dwight guided them to the pegs on the sides of the table, buckling his feet in place. In this position, Jim realized, with his legs bent, ass open and exposed in the air, cock swinging beneath him, and head dangling, Dwight could access any part of him at any time.

“Grab the legs of the bench slave.” Coming around to the front, Dwight produced a roll of duct tape, which he used to secure Jim’s hands in place. “I’ve got a treat for you tonight Jim, since you were so good earlier,” Dwight straightened, running his meaty hands along Jim’s side as he paced back towards Jim exposed anus.

“It’s not quite time for that yet though, first we have a couple things to get out of the way. First, Mose has been pining for you. I don’t think his scarecrow can satisfy him anymore, not after your sweet ass.” To punctuate his words, Dwight pushed one digit against Jim’s hole, not quite entering. He traced that finger down his taint, then up again, back and forth several times before stopping suddenly. “Since you were good, I think you’ve earned a little lubrication.”

Dwight pulled a bottle on lube from his pocket. Popping the cap, the squirted the cold lube onto his hand, coating several fingers. He set the tube down on Jim’s back and rubbed one finger against Jim’s anus before pushing in with a small pop. He worked one finger all the way into Jim’s tight little channel before withdrawing and coming back with two fingers. Dwight really didn’t have the patience for long drawn out prep, working a third finger in. He was too anxious to get on with the show. A few more thrusts and Dwight decided that was enough stretching. He turned to see Mose had already stripped and was practically dancing with anticipation. His ruddy cock was standing at attention, already beading with precum.

With a chuckle, Dwight waved over his cousin, crossing to stand over by Jim’s head again. Mose approached the bound man, excitement nearly over taking him. Gripping either side of Jim’s butt cheeks, Mose thrust his member against Jim’s sensitive perineum. A quiet whine escaped Jim as he couldn’t help but be excited for Mose to shove into him. Jim’s own cock had hardened beneath the table.

“Oh I knew I almost forgot something,” Dwight cried out, looking around hastily. Walking a few quick steps away and back again, he placed a large milking pail beneath Jim’s dick. “There we go, all set,” Dwight gave Mose a thumbs up and without further ado, Mose shoved into Jim.

Jim cried out, a pitiful needy noise that even to him sounded like a bitch. Mose set a breakneck pace, jackhammering into Jim so fast the entire bench shook with the power of it. Every other thrust hit his prostate dead on, sending sparks of arousal up his spine and down his cock. The rough grain of the wood rubbed against his sensitive nipples.

Dwight crouched next to Jim’s hanging head. “You should see how beautiful you look right now, needy and horny. I think I’ll make one of these screenshots my new wallpaper on the work computer.”

Mose knew he couldn’t last much longer. He’d been close to blowing his load just looking at Jim, and now his over-excited cock couldn’t take much more. Jim’s tight ass was heaven, milking his large cock. As Mose continued to drive home into Jim, he threw back his head, reveling in the vice grip that Jim had around his relatively unused dick.

“You’ll never be anything but my plaything Jim. I own you, now and forever, and I’ll share you with everyone. Everyone will hear those pathetic little noises you make, they’ll all see how much you love being used, how good you are at taking cock. I have big plans for you Jim, this is just the beginning.” Dwight continued to whisper into Jim’s ear. “Your ass looks so tight around Mose’s dick, you’re just eating him up. Do you think you can last longer than him Jim? You better, because you don’t have my permission to come yet.”

Jim groaned, he knew Mose couldn’t be long from shooting his load deep inside of him, if his frenzied thrusts were any clue, but his constant assault on Jim’s prostate had him on the edge of an orgasm as well. Over and over, Mose hit the spot, sending endorphins rushing to his brain and precum running down his cock.

“Whatever you do, don’t think about the friction of the table against your nipples. Or about the image of your anus stretching to accommodate Mose.” Dwight leaned in to bite Jim’s ear. “Don’t think about him pounding into you, in and out, in and out, in and out…”

With one last shove, Mose seated himself far inside Jim, shooting out his hot semen. Between that and Dwight’s dirty talk, Jim didn’t have a chance, his own cock spurting wildly into the bucket waiting beneath.

“Damnit Jim, can’t you just follow the rules? I said not to cum, does that mean nothing to you?” Dwight stood up, pacing away from the bench as Jim fought to catch his breath and Mose withdrew from Jim, leaving his hole messy and feeling very empty. Mose wandered out of the barn, leaving Jim and Dwight alone.

“I thought we had an agreement Jim. You can fuck Pam tonight if you were good, if you followed my rules, like a good little slave.” Dwight said.

“I-I’m sorry daddy,” Jim said hoarsely.

“Well now I’ll give you an option Jim. You can both take 20 swats and not have sex with Pam tonight, or you can take 20 swats and have sex with Pam tonight, but wear a butt plug the whole night.” Dwight said, approaching the table again, holding a thin wooden cane in his hands.

Jim’s heart sped up. “I’ll do the second option, daddy.” He said, after only a moment of hesitation. He would’ve liked to think to himself that he chose that for Pam, so he wouldn’t disappoint her, his wife who he loved. But honestly, a deep dark side of him that had been emerging more and more recently, thought that fucking Pam while being filled by a dildo sounded almost too hot. Being filled while he filled Pam… the thought had him hard again.

“I was hoping you’d choose that,” Dwight admitted, with a secret grin. “Now count,” he brought the cane down on Jim’s left butt cheek.

“One,” “Two,” “Three,” Jim ground his teeth and counted, as Dwight peppered blows over Jim’s butt cheeks and upper thighs.  Dwight was rather enjoying seeing Jim’s skin redden under the cane, but his own erection demanded attention, so he hurried this punishment along.

“Twenty,” Jim gasped, relaxing the muscles in his back that had tightened. The sound of a zipper opening was the only warning he had before he was suddenly filled by another cock.

“Ahh,” Jim cried out, feeling his abused anus complaining. Dwight shoved in slowly, seating himself deep within Jim’s inner canal. Jim’s exhausted rectal muscles twitched around Dwight’s cock, sending sensations through both of the men. Dwight withdrew slowly and pushed back in, slow fucking Jim. At first Jim was grateful for the reprieve, but soon the agonizingly slow friction became too much and he started squirming, wishing he had enough leverage to fuck himself silly on Dwight’s pole.

Dwight continued to pump in and out of the bound man on the bench at the same pace, despite his instincts screaming to pound into him and leave him sore for weeks.

“Please Daddy please I need you to fuck me hard please,” Jim begged, the buildup too much for him.

“Bad slaves don’t get what they want.” Dwight responded dispassionately.

“Please, I need you please please please. Daddy…”

Dwight’s resolve was chipping away piece by piece, Jim’s sweet words wearing away at him. He was a sucker for begging. For another 30 seconds, he continued his slow pace, in and out, eliciting groans from a very frustrated Jim. Then, without warning, he let go.

The sudden change of pace made Jim cry out, ripping a scream from his throat. Jim’s already used asshole was protesting this abuse but Jim’s cock didn’t care about that, or apparently the fact that it had just come a few minutes ago. He felt the waves of an orgasm coming on, his cock was jerking already.

“Can I come daddy, please?”

“Yes you may,” Dwight gasped, feeling Jim’s impending orgasm as his channel tightened around Dwight’s hard penis. Slick, hot, and tight, Jim’s ass milked Dwight’s cock. Surrendering himself, Dwight gave one last thrust and gave Jim’s ass a hard slap for good measure.

As both men came down from their orgasms, Dwight pulled out, walking around the table. “Clean it,” he said, standing in front of Jim’s head. Jim could barely lift his head as the aftershocks wracked his body, but he managed to prop his chin on the edge of the bench and lap at Dwight’s shrinking member. The taste of lube mixed with Dwight and Mose’s semen and his own juices was unpleasant, but soon enough, Dwight was satisfied and tucked himself back into his pants.

“Now, I know you’re wondering what your surprise is. Honestly, after you disobeyed me earlier, I debated not giving it to you at all, but it’s as much for me as it is for you,” The sound of the barn door opening again drew Jim’s attention, but his muscles were too weak for him to crane his head around to look. “Oh good, you’re here.”

“What’s going on here Dwight?” Jim heard the familiar voice and groaned, squeezing his eyes shut in shame. “What-who is that? What is this!?”

“Now now Oscar, just come in and I’ll explain.” Dwight said, waving the Hispanic man into the barn. “Jim and I have an arrangement, he pleasures me and in return I didn’t fire him. But I want to share him with others, and I thought we could start with you.”

Oscar’s face was a mix of horror, confusion, intrigue, and arousal. He was horrified to see his friend tied up this way, but he couldn’t deny that seeing his long fit body bound and ready before him wasn’t sending blood rushing south of the border.

Dwight, seeing his accountant’s confusion, explained further. “It’s really ok Oscar, Jim likes being used, isn’t that right slave?”

Jim debated for a moment. On one hand if he told Oscar that he was being used against his will, maybe he could help him get out of the contract. Oscar knew a lot about legal matters…. But Dwight had those video tapes, recordings of him saying some pretty damning things. And if he asked for help, Dwight would surely punish him. Even more though, Jim was surprised to realize he wasn’t being used against his will. He did enjoy being used and abused and he didn’t really want it to end if he was being honest.

“It’s true Oscar, I do like being fucked by men. Dwight owns me, he’s my Daddy.” He said dutifully.

“You heard him Oscar, he loves it. I plan on sharing him with the majority of the people in the office, but I wanted to start with you. For now, you can use his mouth,” Dwight gave Oscar a helpful push towards Jim’s head.

Oscar’s mind was spinning. He’d always been attracted to Jim, his long lean form and that boyish face and now was his chance. Could this really be real, and not a wet dream that he’d soon wake up from, rutting into his sheets? ‘ _I can’t do this, he’s my friend_ ’ Oscar thought to himself. But maybe he does really enjoy this, really want it. In that case, his conscious could stay clean.

Jim could read the apprehension on Oscar’s face. Oscar may be unsure, but Jim knew that if Oscar didn’t fuck his mouth, Dwight would be mad, and a mad Dwight is not good for Jim. So Jim made up his mind.

“It’s ok Oscar, I really want to do this. Make me your bitch Oscar, fuck my mouth hard,” Jim cooed. In an instant, the hesitation in Oscar was gone. Fumbling with his zipper, he couldn’t get his cock out quick enough. Around 7 inches, the Spaniard was sizable, but not as large as Mose or Dwight, giving Jim more confidence.

He opened his mouth, taking in the first few inches of Oscar’s slightly bent cock. He bobbed his head as best he could, bound like he was. Oscar groaned, letting his head fall back as the warm cavern of Jim’s mouth engulfed his now fully erect penis. Jim sucked the head, before going back down to take almost the entire thing in his mouth. Rearing back, he licked down the side of the darker man’s cock, tasting the salt of sweat and feeling the veins in his groin pulsate.

Oscar couldn’t believe it, his office crush was naked and tied up before him, sucking his cock like a pro. Gripping Jim’s hair, he began to thrust into Jim’s mouth, fucking the larger man’s throat. The little gagging noises that Jim made only spurred Oscar on further, increasing his pace. Jim’s nose pressed into Oscar’s groin, smelling sweat and musk as his pubic hair tickled his nose.

As Jim’s throat began to get sore, Oscar picked up the pace, slamming his cock into Jim’s hot mouth, forcing Jim to alternate sucking and breathing. Soon, Oscars cock began to shoot hot salty sum into Jim’s mouth, hitting the back of his throat. Jim swallowed all of it, very aware of Dwight’s watchful eyes.

Oscar slowed down and eventually withdrew from Jim’s mouth, trying to catch his breath. Dwight walked forward, holding a large dildo that he had picked up god knows when. Walking behind Jim, he pressed it into Jim’s burning asshole, popping in the bulbous head and pushing the entire thing into his core.

“Remember Jim, keep this in all night until tomorrow morning. I want to keep you stuffed full of my cum all night long. I’ll remove it tomorrow morning at the office and If you aren’t still full of cum, you will be punished.” Dwight gave the end of the dildo a tap, making it vibrate against his prostate.

Dwight then unbuckled Jim’s feet, ripped off the duct tape from his hands. Gingerly, Jim climbed off of the bench, his sore muscles protesting standing up straight. The dildo in his ass rubbed against his prostate with every movement, it was much larger than the highlighter than Dwight had made him carry inside of him. Dwight ducked down to grab the pail, handing it to Jim.

“Drink it all,” was Dwight’s only command. Jim obeyed, sipping his own lukewarm semen out of the dirty bucket, which gave the fluid a distinct metallic flavoring. He almost retched, but was able to keep the sum down.

“Go get dressed and leave, both of you. I’ll see you at work.”


End file.
